Uses
2-Amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide, is a precursor in the synthesis of Dasatinib (D193600), a protein tyrosine kinase inhibitor, and also for 2-Amino-thiazole-5-carboxylic Acid Phenylamide Derivatives, used as potent and selective anti-tumor drugs.
Synthesis
2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide is synthesised using Tert-butyl (5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-YL)carbamate as a raw material by chemical reaction. The specific synthesis steps are as follows:
To the stirred solution of trifluoroacetic acid (TFA) (250.0 mL) added tert-butyl (5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)carbamate 23 (25.0 g, 0.07 mol) and stirred for 2h at 25-30°C. Reaction completion was confirmed by TLC, distilled the TFA and the residue was diluted with ethyl acetate (EtOAc),(250.0 mL). Ethyl acetate layer was washed with saturated NaHCO3 solution (2 X 25.0 mL), water, followed bysaturated NaCl solution (125.0 mL). Ethyl acetate layer was dried over Na2SO4 and concentrated. The residual mass on treatment with methyl tert-butyl ether (250.0) gave 9 (16.2 g, 89percent) [11].IR (KBr, cm-1): 3382.4, 3284.85 (N-H), 1627.02 (C=O), 1644; 1H NMR spectrum (400 MHz, DMSO-d6), δ, ppm(J, Hz): 9.63 (s, 1H, thiazole-H), 7.86 (s, 1H), 7.60 (s, 2H, -NH2), 7.38 (dd, 1H, J =7.5, 4.02, Ar-H), 7.20-7.22 (m,2H, J =7.5, Ar-H), 2.20 (s, 3H, Ar-CH3); 13C NMR spectrum (100 MHz, DMSO-d6), δ, ppm: 172.2, 159.6, 143.2,138.9, 133.7, 132.5, 129.0, 128.0, 127.0, 120.7 and 18.3; MS (ESI) m/z 268.0 [M + H] + [11].
